Pleasant Prairie, WI Inline Skating Trails and Maps

1315 Reviews

Looking for the best Inline Skating trails around Pleasant Prairie?

Find the top rated inline skating trails in Pleasant Prairie, whether you're looking for an easy short inline skating trail or a long inline skating trail, you'll find what you're looking for. Click on a inline skating trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
61 Results
Activities
Length
Surfaces
Type

Almond Road Bike Path

1.5 mi
State: IL
Asphalt

Bloomingdale Trail (The 606)

2.7 mi
State: IL
Asphalt, Concrete

Busse Woods Trail

11.6 mi
State: IL
Asphalt, Concrete

Chicago Lakefront Trail

19 mi
State: IL
Asphalt, Concrete

Deer Grove Trail

3.9 mi
State: IL
Asphalt

DuPage River Trail

49.3 mi
State: IL
Asphalt

Fox River Trail (IL)

45.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Glacial Drumlin State Trail

53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

H.U.M. Trail

3.5 mi
State: IL
Asphalt

Hank Aaron State Trail

15.2 mi
State: WI
Asphalt, Crushed Stone

Illinois Prairie Path

58.52 mi
State: IL
Asphalt, Concrete, Crushed Stone

KR Trail

1.5 mi
State: WI
Asphalt, Boardwalk

Kenosha County Bike Trail

7.9 mi
State: WI
Asphalt

Kenosha Pike Bike Trail

6.95 mi
State: WI
Concrete

Kuhn Road Trail

1.4 mi
State: IL
Asphalt

Lake Andrea Multi-Use Path

2.3 mi
State: WI
Asphalt

Lake Arlington Walking Path

2 mi
State: IL
Asphalt

Meadowbrook Trail

2.4 mi
State: WI
Concrete

Milwaukee RiverWalk

3.1 mi
State: WI
Concrete

New Berlin Recreation Trail

7 mi
State: WI
Asphalt
Accordion

North Branch Trail

25.5 mi
State: IL
Asphalt

North Central DuPage Regional Trail

11.6 mi
State: IL
Asphalt, Crushed Stone

North Shore Channel Trail

8.3 mi
State: IL
Asphalt, Concrete, Dirt

North Shore Trail (WI)

3 mi
State: WI
Asphalt

Oak Leaf Trail

123.6 mi
State: WI
Asphalt

Ozaukee Interurban Trail

30.1 mi
State: WI
Asphalt

Palatine Trail

9.6 mi
State: IL
Asphalt, Concrete

Pike River Pathway

6.9 mi
State: WI
Asphalt

Poplar Creek Trail

9.5 mi
State: IL
Asphalt

Prairie Trail (IL)

26.4 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Salt Creek Trail (IL)

30.4 mi
State: IL
Asphalt, Cinder, Woodchips

Valley Line Trail

1.1 mi
State: IL
Asphalt

West Allis Cross Town Connector

0.9 mi
State: WI
Asphalt

Beerline Trail

3.7 mi
State: WI
Asphalt

Chain O' Lakes Bike Path

3.2 mi
State: IL
Asphalt

Fox River Trail (WI)

6 mi
State: WI
Asphalt

Green Bay Trail

6.5 mi
State: IL
Asphalt, Concrete, Crushed Stone

Lake Country Trail

16.7 mi
State: WI
Asphalt

North Shore Bike Path

7.7 mi
State: IL
Asphalt, Crushed Stone

Powerline Trail (WI)

4.4 mi
State: WI
Asphalt

Randall Road Bike Trail

3.9 mi
State: IL
Asphalt

Robert McClory Bike Path

25.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Root River Pathway

6.6 mi
State: WI
Asphalt

Seven Waters Bike Trail

18.6 mi
State: WI
Asphalt, Crushed Stone, Gravel

Skokie Valley Trail (Lake County)

9.8 mi
State: IL
Asphalt

Stone Mill Trail

1.5 mi
State: IL
Asphalt

Techny Trail

3 mi
State: IL
Asphalt, Concrete

East Northbrook Trail

1.1 mi
State: IL
Asphalt

Kinnickinnic River Trail

2.3 mi
State: WI
Asphalt

Prospect Heights Bike Path

4.2 mi
State: IL
Asphalt

Ridgefield Trace

8 mi
State: IL
Asphalt

Lake Geneva Bike Path

8.9 mi
State: WI
Asphalt

Bull Valley Road Shared-Use Path

1.1 mi
State: IL
Asphalt

Fort Hill Bike Path

2.4 mi
State: IL
Asphalt

Lies Road Trail

2.8 mi
State: IL
Asphalt

Racine County Bike Trail

1.4 mi
State: WI
Asphalt, Concrete

Racine-Sturtevant Trail

3.5 mi
State: WI
Asphalt
Trail Image Trail Name States Length Surface Rating
This bike path sits on the east side of Almond Road between Washington Street and Fairfield Lane in Gurnee. The 8-foot wide asphalt path is used by residents as a spot for exercise and recreation, but...
IL 1.5 mi Asphalt
The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail trail on Chicago’s northwest side. Built on a former rail line, the trail sits 17 feet above four of the city’s...
IL 2.7 mi Asphalt, Concrete
The Busse Woods Trail spans the Ned Brown Forest Preserve, a 3,700-acre natural space in the northwestern suburbs of Chicago. The preserve—popularly just called Busse Woods—has a large meandrous lake...
IL 11.6 mi Asphalt, Concrete
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago to pass many cultural and tourist attractions throughout the...
IL 19 mi Asphalt, Concrete
The Deer Grove Trail is one of several great Chicagoland trails located in properties of the Forest Preserve of Cook County. Deer Grove is the oldest of all the Cook County preserves. It's comprised...
IL 3.9 mi Asphalt
The DuPage River Trail spans 49.3 miles across two counties: DuPage and Will. The trail is open in several disconnected segments mainly in parks and forest preserves beginning in Bartlett and...
IL 49.3 mi Asphalt
The Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin; Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude of...
IL 45.7 mi Asphalt, Concrete, Crushed Stone
The 53-mile Glacial Drumlin State Trail between Cottage Grove and Waukesha provides a glimpse into the past when glaciers bore down on southeastern Wisconsin in the last Ice Age. Those gigantic sheets...
WI 53.2 mi Asphalt, Crushed Stone, Gravel
The H.U.M. Trail (a.k.a. the Huntley-Union-Marengo Trail) was planned to link all three of its namesake northern Illinois towns, but so far only connects Marengo and Union. Interestingly, the...
IL 3.5 mi Asphalt
The Hank Aaron State Trail, which spans the breadth of Milwaukee County, begins at Lakeshore State Park in Milwaukee, where it overlooks Lake Michigan to the east and provides breathtaking views of...
WI 15.2 mi Asphalt, Crushed Stone
The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. The 58-mile trail consists of five connected trail segments with three main branches that converge at 300 S...
IL 58.52 mi Asphalt, Concrete, Crushed Stone
The KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha Pike Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
WI 1.5 mi Asphalt, Boardwalk
The Kenosha County Bike Trail runs for nearly 8 miles in two sections separated by couple miles with the city of Kenosha. About the Route The northern segment runs between 1st St....
WI 7.9 mi Asphalt
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
WI 6.95 mi Concrete
The Kuhn Road Trail starts on Lies Road, at Glenbard North High School and continues south along Kuhn Road, past single-family homes and Friendship Park. The trail officially ends at Barbara O'Rahilly...
IL 1.4 mi Asphalt
The 2.3-mile multiuse trail wraps around Lake Andrea in Pleasant Springs Park. The trail is an easy walk, run or ride around the lake, and is accessible for a wide range of users. It also helps users...
WI 2.3 mi Asphalt
Lake Arlington is an artificial lake and popular recreation area in Arlington Heights in Cook County. The park features amenities to interest visitors of all ages and it is a local favorite for family...
IL 2 mi Asphalt
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
WI 2.4 mi Concrete
The Milwaukee RiverWalk provides a pleasant way to get around Milwaukee from the Historic Third Ward, through downtown, and north to the Lower East Side. It also has easy connections to three other...
WI 3.1 mi Concrete
The paved New Berlin Recreation Trail runs straight as an east-west compass bearing for 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. While it is void of trestles,...
WI 7 mi Asphalt
Accordion
The North Branch Trail follows the North Branch of the Chicago River for 25.5 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
IL 25.5 mi Asphalt
The North Central DuPage Regional Trail stretches 11.6 miles in four segments between the communities of Wayne in the west and Roselle in the east. This paved, multiuse trail provides residents and...
IL 11.6 mi Asphalt, Crushed Stone
The North Shore Channel Trail extends 8.3 miles from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in...
IL 8.3 mi Asphalt, Concrete, Dirt
Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
WI 3 mi Asphalt
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for 123 miles in and around the city of Milwaukee on a changing terrain of flat rural...
WI 123.6 mi Asphalt
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
WI 30.1 mi Asphalt
The village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...
IL 9.6 mi Asphalt, Concrete
The Pike River Pathway is a paved, multiuse trail that parallels the river after which its named through meadows, fields, woods, and residential areas in the Village of Mount Pleasant, WI.  From...
WI 6.9 mi Asphalt
The Poplar Creek Trail is a 9.5-mile paved loop around Poplar Creek Forest Preserve near Hoffman Estates. The trail has a couple of hills but is otherwise level and makes for a pleasant journey...
IL 9.5 mi Asphalt
The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail trail spans just over 26 miles from the Wisconsin border and the farms and...
IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
The Salt Creek Trail travels 28.6 miles between the Busse Woods Forest Preserve and the Brookfield Zoo. Along the way, it connects several beautiful county forest preserves and other woodland...
IL 30.4 mi Asphalt, Cinder, Woodchips
The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
IL 2 mi Asphalt
Just 1 mile long, the Valley Line Trail—also known as the Sauganash Trail—extends between Bryn Mawr Avenue and Devon Avenue in the Chicago neighborhood of Sauganash. Two bridges allow for safe...
IL 1.1 mi Asphalt
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. The trail leaves from a junction with the New Berlin...
WI 0.9 mi Asphalt
The Beerline Trail, named after the corridor that was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, runs for 3.7 miles through central...
WI 3.7 mi Asphalt
The Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
IL 3.2 mi Asphalt
The Fox River Trail runs diagonally along its namesake waterway through Waukesha in southeastern Wisconsin (just outside of Milwaukee). The trail is part of the Route of the Badger, a Milwaukee-area...
WI 6 mi Asphalt
The 6.5-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park, and...
IL 6.5 mi Asphalt, Concrete, Crushed Stone
The 16.2 mile Lake Country Trail runs from the western edge of Waukesha to Oconomowoc in Wisconsin’s Lake Country area. Most of the trail was built on a former Milwaukee-Watertown Interurban Railway...
WI 16.7 mi Asphalt
The North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. About the Route The trail is one of dozens in the...
IL 7.7 mi Asphalt, Crushed Stone
The Paul Douglas and Crabtree Preserve Trail System connects two large nature preserves in northwestern Cook County. The trail begins at the Old Stover Trailhead in the Crabtree Preserve, near the...
IL 9.2 mi Asphalt
Stretching east-west through the City of Greenfield, the Powerline Trail is a new shared-use path that offers multiple recreation and transportation opportunities for locals and visitors alike. The...
WI 4.4 mi Asphalt
The Randall Road Bike Trail offers a 4-mile paved north-south route along its namesake roadway in a suburb west of Chicago. A highlight of the journey is the trail's passage through the LeRoy Oakes...
IL 3.9 mi Asphalt
The 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along the...
IL 4.4 mi Asphalt
The Robert McClory Bike Path runs the length of Lake County, knitting together a string of communities on the north shore of Chicago all the way to the Wisconsin border. In 1997, the trail was named...
IL 25.4 mi Asphalt, Concrete, Crushed Stone
The Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
WI 6.6 mi Asphalt
The Seven Waters Bike Trail is a scenic corridor stretching more than 18 miles north–south between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails, locally...
WI 18.6 mi Asphalt, Crushed Stone, Gravel
The Skokie Valley Trail connects Highland Park in the south to the northern trailhead in Lake Bluff. The entire trail corridor is a rail-with-trail, paralleled by double tracks that sit about 40 feet...
IL 9.8 mi Asphalt
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
IL 1.5 mi Asphalt
The Techny Trail links downtown Glenview, a charming village northwest of Chicago, with the Techny Basin, a scenic wetlands area adjacent to the West Fork of the Chicago River's North Branch....
IL 3 mi Asphalt, Concrete
The Union Pacific Trail, otherwise referred to as the Weber Spur Trail, offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. About the...
IL 1.2 mi Asphalt
The East Northbrook Trail is a 1-mile route through a wooded corridor adjacent to an out-of-service rail corridor in the Village of Northbrook. The trail provides access to residential neighborhoods,...
IL 1.1 mi Asphalt
Kinnickinnic River Trail (called the KK River Trail by locals) runs just over 2 miles in southern Milwaukee, following the river through a densely populated and industrial corridor. The trail links...
WI 2.3 mi Asphalt
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
IL 4.2 mi Asphalt
The Ridgefield Trace is a multi-use pathway that runs through suburban Crystal Lake, Illinois. The trail takes its name from the original Indian trace that once ran along the route of what is now...
IL 8 mi Asphalt
The 8.9-mile Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. The Lake Geneva Bike...
WI 8.9 mi Asphalt
The Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
IL 1.1 mi Asphalt
The Fort Hill Bike Path trail sits on the north side of Peterson Road/ County Road 20. The trail peels away from the Prairie Crossing Bike Path at Midlothian Road and extends west, passing industries...
IL 2.4 mi Asphalt
This shared-use path runs east-west through the village of Carol Stream in Du Page county. Sitting on the grassy north side of Lies Road between Fair Oaks Road and Gary Avenue, the path is used as an...
IL 2.8 mi Asphalt
Helping to extend the excellent network of trails around the city of Racine deeper west into the heart of the county, the Racine County Bike Trail serves as a disconnected addition to the...
WI 1.4 mi Asphalt, Concrete
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
WI 3.5 mi Asphalt

Recent Trail Reviews

Glacial Drumlin State Trail

Beautiful sunny October ride

October, 2026 by redpine2001

Completed my final leg of this trail by riding from London to Cottage Grove today. Trail conditions were very good, however the bridges can use some maintenance. All have matting across them to assist in preventing flats, however watch your approach, there can be some serious bumps getting onto & off the bridges. Having ridden the entire trail now, eastern portion several times; it’s just my opinion that the western portion would be my recommendation. East of Douseman the trail is paved, however much of it is in need of maintenance to remedy cracks.

White River State Trail

Pleasant Surprise

September, 2026 by dsjr2

Scenic, very pleasant ride today. Farmland, lots of bridges, packed gravel so no surprises. Parked at the Elkhorn trailhead and biked to Burlington and back. Note: the DNR site says there's a bridge out, as of 9/27/26 - there are no bridges out. Really nice ride and great way to spend a 70 degree and sunny day in late September.

Fox River Trail (IL)

Wonderful Trail

September, 2026 by nevogamer_tl

We rode the Fox River Trail over two days in September 2026. We did a short ride from St Charles to South Elgin and back one the first day, followed by a ride to Aurora and then on to part of the Illinois Prairie Path before returning to St Charles. The trail was in excellent shape and, for the most part, was well marked. We thought the scenery was better going south, with lots of water fowl, flowers and points of interest to enjoy. This trail lived up to its expectations.

Accordion

Robert McClory Bike Path

September 2026 Ride

September, 2026 by dpott

I just rode from my Chicago home to Racine on the North Shore Channel, Green Bay, R McClory and Kenosha County trails. The McClory is newly paved and well signed from the Great Lakes Naval Station north to the state line. There are no facilities other than the occasional bench, and there are long stretches without any shade. Otherwise it is a terrific ride!

Kenosha Pike Bike Trail

Spectacular Lake Views

September, 2026 by kriekkoff_tl

The trail starts unassumingly in a residential neighborhood to the north and winds its way through Carthage College before bursting out of a canopy of trees into a spectacular, unobstructive view of Lake Michigan. The trail hugs the coast and meanders through a series of gorgeous parks. Just when your senses have almost reached their limit, you find yourself riding along Harbor Park filled with an assortment of sculptures, museums, and marinas. The Park is electric!
This was the most enjoyable ride I have ever taken. I will be back!
There are two cautionary notes, however.
1. The city roads between Poerio Park West and upper Alford Park are in horrible condition. Maybe avoid this northern section altogether.
2. The trail that goes south from the 50th Street bridge as you enter the Harbor is actually a staircase. I missed it the first time, but realized it on my return. There is a very steep embankment with a thin bike path next to the stairs, if you want to risk it.

North Shore Trail (WI)

Short, flat and easy to ride

September, 2026 by kriekkoff_tl

The 10-foot wide asphalt surface is still in good shape. The trail hugs the road at the north end, but eventually disappears behind suburban backyards under a wonderful canopy of trees. There are a few pesky road crossings, but not bad. The trail is short, but flat and easy to ride. This is a great connector to the Kenosha County Bike Trail or the Kenosha Pike Bike Trail.

Millennium Trail (IL)

Hill Billy - Part 2

September, 2026 by kriekkoff_tl

I almost forgot to include this in my previous review:
If you do not like hills, DO NOT do either section of this trail.

Millennium Trail (IL)

Hill Billy

September, 2026 by kriekkoff_tl

Both the North and South sections used asphalt and crushed stone surfaces. Care must be taken when riding on the crushed stone. The trail is nearly 12 foot wide and it is neatly groomed, however, the stone is just loose enough to keep bicycle speeds down. The rider who tests their speed traveling downhill and around the blind curves will surely tumble. The age of the asphalt in both sections varies from "newer" to "desperately in need of repair." The southern section actually has a warning sign just south of Fairfield Park.
The last two miles of the northern section in Round Lake Beach is loaded with perpendicular cracks in the asphalt causing a jarring ride even at slow speeds.
One must be cautious at the street crossings although some of the busier roads have traffic lights with designated pedestrian cross walks. The signage was ok, but could have been better.

Robert McClory Bike Path

New Asphalt!

September, 2026 by kriekkoff_tl

Except for the 2 miles of crushed stone from Sheridan Road in Highland Park to County Line Road in Ravinia, the entire trail surface it asphalt!
The first 11 miles of the trail from the Wisconsin border is newer asphalt; no cracks or bumps to worry about. Just a smooth ride. The northern section of the bike path, however, is plagued with several street crossings, all of which must be approached with caution. There is little to no shade on the northern section.
The southern section of the bike path has a lot more points of interest including various sculptures along the trail, Metra train stations, the Ravinia Festival grounds and interesting cities to explore. The southern section offers much more shade, but also has a few street crossings as well.
The trail does give way to the road in both sections, but the signage is good for the most part. There are new mile markers on the west side of the trail every 1/2 mile.

Muskego Recreation Trail

Nice East-West Corridor

September, 2026 by kriekkoff_tl

The surface of this 8-foot wide trail seems to be crushed stone over an older asphalt base. It is a little tougher to ride than the typical crushed gravel surface. There are some "soft" spots throughout the length of the route, but still manageable. The trail is relatively flat with an occasional grade change. The scenery is mostly suburban backyard with a touch of industrial to the west. There is very little shade to protect you from the sun, but the openness is refreshing. Although most street crossings have minimal traffic, please take caution when approaching them. This is one of my "go to" rides.

Powerline Trail (WI)

Excellent Off Street Trail

September, 2026 by jjg2

I accessed the Powerline Trail at Cold Spring Road off of the Oak Leaf Trail. My ride on the new trail was very enjoyable and I found the route to be very pleasant passing by a number of neighborhoods. Compliments to the City of Greenfield and We Energies for their efforts to build this trail.

Seven Waters Bike Trail

Vietnam Base Camp

August, 2026 by kriekkoff_tl

The route has a mix of crushed gravel at both ends and a nice wide asphalt trail in the middle. Be careful going through Saller Woods in the village of Rochester. The trail has been scarred by runoff, the gravel is loose and the hills are steep. Like a child clutching tightly to it's mother, the trail hugs Highway 36 for much of the ride. Although most of the trail is concealed by trees and brush, the sound of cars could still be heard. The trail in Burlington ends at a very nice park that has bathroom facility, water fountain and picnic tables under cover for a nice place to have lunch. The best part of the trail was "The Bunker." This bar & grill has a unique military-theme inside and outside its walls including a Vietnam Guard Tower and other military equipment.

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